I've been retired now for about 8 years. Earlier would have been too early for me and I would have liked to phase out or work three or four years longer. I enjoyed my work, loved it in fact but the time came to hang up my spurs. The writing was on the wall in a transition I did not want to make. After 40 years I went back to the farm. That was always my plan but I considered others. I am happy I did this. I have a list of meaningful to-do for the rest of my life and hobbies I enjoy but seldom partake of. I see the result of my labor every day and it is good. Everything I do makes an improvement. I don't see my attitude changing just my ability to get things done. Meanwhile, I enjoy a good tired from my labor most evenings and some days I just do something else I want to do.
I have never played golf, never taken a cruise and don't want to, I don't own a single pastel shirt and I don't play any sort of games at all. In my work I traversed the world many times. My wife does not want to travel far, three days is about her limit, and with the mess that goes on traveling these days you could not pay me enough to get on an airplane. We have an Airstream but don't use it. The best part of any trip is coming in the front gate.
My late Dad planned to work to 70, he made it to 67 when his position was abolished. His secretary received the notification by fax from a guy he had mentored and sponsored. He lived another 10 years. They made a great bet on his pension. I don't have one, saved every penny myself and don't figure on being able to spend it all sanely. I started early and never let up but I do wish I had known a whole lot more about investing than I did. We inherited very little in possessions and I paid the heirs for 3/4 of the place I didn't already own. I do have the good reputation my parents left me and I treasure that as all I expected them to leave me. Time will tell but we have three levels of retirement savings and we live on one. I am not smug and not completely comfortable. I think it is important to maintain some tension. We still need to manage our investments.
I could have worked and built the company back after the last bust in the oilfield. I've done enough of that though. At least 9 busts in 40 years is enough. My engineering business was based on good work and relationships. My peer group had just about all left the business. The rules changed and I didn't need or want to play by them any longer. It all became a lot less fun.
One bucket for money, one bucket for crap. When one bucket gets full, you go home. So I did.
If you don't have something to retire to just don't do it. You either wear out or rust out.
If your are not self-driven you may need to stick with the carrot and whip as long as you can. It never was for me, being directed by others. Leave no doubt, we are all directed in some way by others just not all of us fit in that 30 years and a gold watch same ball and chain every day or taking a bullet in the back of the head and not even hearing the shot or knowing where it came from. In some places the financial rewards and being taken care of can be pretty sweet. I tried it for part of my career, not worth the price of poker eventually. I solved problems, hardly ever did the same thing twice in a row, I turned some jobs down that were just not worth doing or doing for someone I didn't need to deal with.
I have a friend who retired in 2018. He was in sales. I told him much of what I've just said. Retire to something most particularly. He didn't and he is dying.
That was a very useful and thoughtful post. Glad you took the time to write it. Kudos... no sarcasm.